HUP9903226A2 - Process for producing mycophenolic acid and derivatives thereof - Google Patents

Process for producing mycophenolic acid and derivatives thereof Download PDF

Info

Publication number: HUP9903226A2
Authority: HU; Hungary
Prior art keywords: mycophenolic acid; culture; general formula; group; penicillium
Prior art date: 1999-09-23

Application number

HU9903226A

Other languages

English (en)

Hungarian (hu)

Inventor

Attila Konya

Istvan Barta

Antalne Dr Jekkel

Gyoergy Somogyi

Ambrus Gabor Dr

Horvath Gyula Dr

Suetoe Julianna Mozesne

Szabo Antal Dr

Szabo Istvan Mihaly Dr

Janos Salat

Sandor Boros

Original Assignee

Gyogyszerki

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-09-23

Filing date

1999-09-23

Publication date

2002-08-28

1999-09-23 Application filed by Gyogyszerki filed Critical Gyogyszerki

1999-09-23 Priority to HU9903226A priority Critical patent/HUP9903226A2/hu

1999-11-29 Publication of HU9903226D0 publication Critical patent/HU9903226D0/hu

2000-09-22 Priority to KR1020027003830A priority patent/KR20020060184A/ko

2000-09-22 Priority to DK00966338T priority patent/DK1216237T3/da

2000-09-22 Priority to ES00966338T priority patent/ES2211620T3/es

2000-09-22 Priority to EP00966338A priority patent/EP1216237B1/de

2000-09-22 Priority to AT00966338T priority patent/ATE256674T1/de

2000-09-22 Priority to DE60007338T priority patent/DE60007338T2/de

2000-09-22 Priority to PCT/HU2000/000099 priority patent/WO2001021607A2/en

2000-09-22 Priority to CA002385317A priority patent/CA2385317A1/en

2000-09-22 Priority to AU76776/00A priority patent/AU768773B2/en

2000-09-22 Priority to JP2001524986A priority patent/JP3854866B2/ja

2000-09-22 Priority to PT00966338T priority patent/PT1216237E/pt

2002-08-28 Publication of HUP9903226A2 publication Critical patent/HUP9903226A2/hu

2004-02-20 Priority to AU2004200673A priority patent/AU2004200673A1/en

2004-03-26 Priority to AU2004201294A priority patent/AU2004201294A1/en

Links

238000000034 method Methods 0.000 title claims description 11
HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 title description 46
HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 title description 41
229960000951 mycophenolic acid Drugs 0.000 title description 41
238000000855 fermentation Methods 0.000 claims description 26
230000004151 fermentation Effects 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
244000005700 microbiome Species 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
241000985504 Penicillium waksmanii Species 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 6
238000011160 research Methods 0.000 claims description 6
241000946782 Streptomyces resistomycificus Species 0.000 claims description 5
241000187180 Streptomyces sp. Species 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
230000002906 microbiologic effect Effects 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
230000001580 bacterial effect Effects 0.000 claims description 4
230000002538 fungal effect Effects 0.000 claims description 2
239000000203 mixture Substances 0.000 description 21
239000002609 medium Substances 0.000 description 17
229920001817 Agar Polymers 0.000 description 16
239000008272 agar Substances 0.000 description 16
239000000047 product Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000008103 glucose Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002054 inoculum Substances 0.000 description 12
241000228143 Penicillium Species 0.000 description 11
239000000725 suspension Substances 0.000 description 11
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000012153 distilled water Substances 0.000 description 7
238000001819 mass spectrum Methods 0.000 description 7
230000001954 sterilising effect Effects 0.000 description 7
238000004659 sterilization and disinfection Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229940041514 candida albicans extract Drugs 0.000 description 6
239000000284 extract Substances 0.000 description 6
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
239000012138 yeast extract Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000228145 Penicillium brevicompactum Species 0.000 description 4
239000003463 adsorbent Substances 0.000 description 4
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
235000013305 food Nutrition 0.000 description 4
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
238000003898 horticulture Methods 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000002245 particle Substances 0.000 description 4
239000013587 production medium Substances 0.000 description 4
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
239000008399 tap water Substances 0.000 description 4
235000020679 tap water Nutrition 0.000 description 4
UKIDUMMXBQMTKO-UHFFFAOYSA-N 1-methyl-1-nitro-2-nitrosoguanidine Chemical compound [O-][N+](=O)N(C)C(=N)NN=O UKIDUMMXBQMTKO-UHFFFAOYSA-N 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical group C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
239000001888 Peptone Substances 0.000 description 3
108010080698 Peptones Proteins 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
229910052921 ammonium sulfate Inorganic materials 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
LFCFXZHKDRJMNS-UHFFFAOYSA-L magnesium;sulfate;hydrate Chemical compound O.[Mg+2].[O-]S([O-])(=O)=O LFCFXZHKDRJMNS-UHFFFAOYSA-L 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
235000019796 monopotassium phosphate Nutrition 0.000 description 3
235000019319 peptone Nutrition 0.000 description 3
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 3
239000000049 pigment Substances 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000758 substrate Substances 0.000 description 3
239000005720 sucrose Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
229910001868 water Inorganic materials 0.000 description 3
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 2
VWFJDQUYCIWHTN-YFVJMOTDSA-N 2-trans,6-trans-farnesyl diphosphate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CO[P@](O)(=O)OP(O)(O)=O VWFJDQUYCIWHTN-YFVJMOTDSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
VWFJDQUYCIWHTN-UHFFFAOYSA-N Farnesyl pyrophosphate Natural products CC(C)=CCCC(C)=CCCC(C)=CCOP(O)(=O)OP(O)(O)=O VWFJDQUYCIWHTN-UHFFFAOYSA-N 0.000 description 2
229930091371 Fructose Natural products 0.000 description 2
239000005715 Fructose Substances 0.000 description 2
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 2
PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
241001123663 Penicillium expansum Species 0.000 description 2
241000864371 Penicillium viridicatum Species 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 2
MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
229960001570 ademetionine Drugs 0.000 description 2
235000011130 ammonium sulphate Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000000843 anti-fungal effect Effects 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000006285 cell suspension Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
238000011161 development Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
PRKAMQKRPBLSND-UHFFFAOYSA-N hydroxymethylmycophenolic acid amide Natural products OC1=C(CC=C(C)CCC(N)=O)C(OC)=C(CO)C2=C1C(=O)OC2 PRKAMQKRPBLSND-UHFFFAOYSA-N 0.000 description 2
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
239000006870 ms-medium Substances 0.000 description 2
WWOOEYCTHQFRGE-UHFFFAOYSA-N mycophenolic acid amide Natural products OC1=C(CC=C(C)CCC(N)=O)C(OC)=C(C)C2=C1C(=O)OC2 WWOOEYCTHQFRGE-UHFFFAOYSA-N 0.000 description 2
229910000069 nitrogen hydride Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 2
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239000002904 solvent Substances 0.000 description 2
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DHPZTYWSWZIJME-UHFFFAOYSA-N 1-(6-hydroxy-2,3-dimethoxy-4-phenylmethoxyphenyl)ethanone Chemical compound C1=C(O)C(C(C)=O)=C(OC)C(OC)=C1OCC1=CC=CC=C1 DHPZTYWSWZIJME-UHFFFAOYSA-N 0.000 description 1
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101710088194 Dehydrogenase Proteins 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
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RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
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BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
229960003390 magnesium sulfate Drugs 0.000 description 1
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XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
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239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical group O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
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NGFMICBWJRZIBI-UJPOAAIJSA-N salicin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1CO NGFMICBWJRZIBI-UJPOAAIJSA-N 0.000 description 1
229940120668 salicin Drugs 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
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CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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159000000000 sodium salts Chemical class 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Health & Medical Sciences (AREA)
General Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Microbiology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)

HU9903226A 1999-09-23 1999-09-23 Process for producing mycophenolic acid and derivatives thereof HUP9903226A2 (en)

Priority Applications (14)

Application Number	Priority Date	Filing Date	Title
HU9903226A HUP9903226A2 (en)	1999-09-23	1999-09-23	Process for producing mycophenolic acid and derivatives thereof
PT00966338T PT1216237E (pt)	1999-09-23	2000-09-22	Processo para a preparacao de acido micofenolico e seus derivados
DE60007338T DE60007338T2 (de)	1999-09-23	2000-09-22	Verfahren zur herstellung von mycophenolsäure und derivaten davon
CA002385317A CA2385317A1 (en)	1999-09-23	2000-09-22	Process for the preparation of mycophenolic acid and derivatives thereof
ES00966338T ES2211620T3 (es)	1999-09-23	2000-09-22	Procedimiento para preparar acido micofenolico y derivados del mismo.
EP00966338A EP1216237B1 (de)	1999-09-23	2000-09-22	Verfahren zur herstellung von mycophenolsäure und derivaten davon
AT00966338T ATE256674T1 (de)	1999-09-23	2000-09-22	Verfahren zur herstellung von mycophenolsäure und derivaten davon
KR1020027003830A KR20020060184A (ko)	1999-09-23	2000-09-22	마이코페놀산 및 이의 유도체의 제조방법
PCT/HU2000/000099 WO2001021607A2 (en)	1999-09-23	2000-09-22	Process for the preparation of mycophenolic acid and derivatives thereof
DK00966338T DK1216237T3 (da)	1999-09-23	2000-09-22	Proces til fremstilling af mycophenolsyre og derivater deraf
AU76776/00A AU768773B2 (en)	1999-09-23	2000-09-22	Process for the preparation of mycophenolic acid and derivatives thereof
JP2001524986A JP3854866B2 (ja)	1999-09-23	2000-09-22	ミコフェノール酸およびその誘導体の製造方法
AU2004200673A AU2004200673A1 (en)	1999-09-23	2004-02-20	Process for the preparation of mycophenolic acid and derivatives thereof
AU2004201294A AU2004201294A1 (en)	1999-09-23	2004-03-26	Process for the preparation of mycophenolic acid and derivatives thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU9903226A HUP9903226A2 (en)	1999-09-23	1999-09-23	Process for producing mycophenolic acid and derivatives thereof

Publications (2)

Publication Number	Publication Date
HU9903226D0 HU9903226D0 (en)	1999-11-29
HUP9903226A2 true HUP9903226A2 (en)	2002-08-28

Family

ID=89999424

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU9903226A HUP9903226A2 (en)	1999-09-23	1999-09-23	Process for producing mycophenolic acid and derivatives thereof

Country Status (12)

Country	Link
EP (1)	EP1216237B1 (de)
JP (1)	JP3854866B2 (de)
KR (1)	KR20020060184A (de)
AT (1)	ATE256674T1 (de)
AU (1)	AU768773B2 (de)
CA (1)	CA2385317A1 (de)
DE (1)	DE60007338T2 (de)
DK (1)	DK1216237T3 (de)
ES (1)	ES2211620T3 (de)
HU (1)	HUP9903226A2 (de)
PT (1)	PT1216237E (de)
WO (1)	WO2001021607A2 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9376415B2 (en)	2009-03-30	2016-06-28	Nippon Suisan Kaisha, Ltd.	Tricyclic condensed heterocyclic compound, process of producing same, and use thereof

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0124953D0 (en) *	2001-10-17	2001-12-05	Novartis Ag	Organic Compounds
WO2003106690A1 (en) *	2002-06-18	2003-12-24	Biocon India Limited	Fed batch solid state fermentation for the production of mycophenolic acid
WO2004087938A1 (ja) *	2003-03-31	2004-10-14	Meiji Seika Kaisha, Ltd.	新規生理活性物質ｐｆ１２７０ａ、ｂおよびｃ物質
MXPA06005659A (es) *	2004-04-26	2007-04-10	Teva Gyogyszergyar Zartkoruen	Proceso para preparacion de acido micofenolico y derivados de ester del mismo.
EP1740563A2 (de)	2004-04-27	2007-01-10	Teva Gyógyszergyár Zártköruen Muködo Részvenytarsaság	Mykophenolatmofetilverunreinigung
US7439373B2 (en)	2004-07-20	2008-10-21	TEVA Gyógyszergyár Zártkörúen Múködö Részvénytársaság	Crystalline mycophenolate sodium
EP1624070A1 (de) *	2004-08-05	2006-02-08	Tecnimede-Sociedade Tecnico-Medicinal, S.A.	Verfahren zur Herstellung von Mycophenolsäure
WO2008003637A2 (en) *	2006-07-05	2008-01-10	Dsm Ip Assets B.V.	Isolation and use of amine salts of mycophenolic acid
US20110166347A1 (en) *	2008-09-10	2011-07-07	Ipca Laboratories Ltd.	Process for preparation of mycophenolic acid, its salt and ester derivatives
CN103641809B (zh) *	2013-11-23	2016-04-13	浙江师范大学	新月旋孢酸类化合物c及其制法和用途
CN109929890B (zh) *	2019-05-08	2020-12-04	广东蓝宝制药有限公司	一种麦考酚酸的发酵工艺
CN115215902B (zh) *	2021-04-21	2024-08-09	中国科学院成都生物研究所	一种具有抗炎活性的水溶性红色食用真菌色素及其制备方法和用途
CN113717888B (zh) *	2021-08-30	2023-03-24	中国热带农业科学院海口实验站	一种新链霉菌及其应用

1999
- 1999-09-23 HU HU9903226A patent/HUP9903226A2/hu unknown
2000
- 2000-09-22 WO PCT/HU2000/000099 patent/WO2001021607A2/en not_active Ceased
- 2000-09-22 AU AU76776/00A patent/AU768773B2/en not_active Ceased
- 2000-09-22 DE DE60007338T patent/DE60007338T2/de not_active Expired - Fee Related
- 2000-09-22 AT AT00966338T patent/ATE256674T1/de not_active IP Right Cessation
- 2000-09-22 KR KR1020027003830A patent/KR20020060184A/ko not_active Ceased
- 2000-09-22 JP JP2001524986A patent/JP3854866B2/ja not_active Expired - Fee Related
- 2000-09-22 ES ES00966338T patent/ES2211620T3/es not_active Expired - Lifetime
- 2000-09-22 PT PT00966338T patent/PT1216237E/pt unknown
- 2000-09-22 CA CA002385317A patent/CA2385317A1/en not_active Abandoned
- 2000-09-22 EP EP00966338A patent/EP1216237B1/de not_active Expired - Lifetime
- 2000-09-22 DK DK00966338T patent/DK1216237T3/da active

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9376415B2 (en)	2009-03-30	2016-06-28	Nippon Suisan Kaisha, Ltd.	Tricyclic condensed heterocyclic compound, process of producing same, and use thereof

Also Published As

Publication number	Publication date
JP3854866B2 (ja)	2006-12-06
KR20020060184A (ko)	2002-07-16
AU7677600A (en)	2001-04-24
DE60007338T2 (de)	2004-11-11
ES2211620T3 (es)	2004-07-16
ATE256674T1 (de)	2004-01-15
WO2001021607A3 (en)	2001-09-07
EP1216237B1 (de)	2003-12-17
HU9903226D0 (en)	1999-11-29
CA2385317A1 (en)	2001-03-29
DK1216237T3 (da)	2004-04-19
PT1216237E (pt)	2004-04-30
AU768773B2 (en)	2004-01-08
JP2003509508A (ja)	2003-03-11
WO2001021607A2 (en)	2001-03-29
EP1216237A2 (de)	2002-06-26
DE60007338D1 (de)	2004-01-29

Publication	Publication Date	Title
KR830002329B1 (ko)	1983-10-22	모나콜린 k의 제조방법
HUP9903226A2 (en)	2002-08-28	Process for producing mycophenolic acid and derivatives thereof
EP0926242A1 (de)	1999-06-30	Gliotoxin-derivate und ein sie enthaltendes antikrebsmittel.
US5276055A (en)	1994-01-04	Antibiotic agents
EP0110710A2 (de)	1984-06-13	Antibiotikum TAN-420, dessen Herstellung und Anwendung
EP1033370B1 (de)	2004-05-12	Substanz ft-0554 und verfahren zu ihrer herstellung
US5008187A (en)	1991-04-16	Antifungal fermentation product
JPH02245191A (ja)	1990-09-28	６―α―ヒドロキシメチルロバスタチン誘導体の製造方法
EP0917587A1 (de)	1999-05-26	Eine neue methode für die herstellung des pravastatin-vorläufers, ml-236b.
US5304485A (en)	1994-04-19	Antibiotic producing microorganism
US3986928A (en)	1976-10-19	Antibiotic a-32390 and process for preparation thereof
US3979433A (en)	1976-09-07	1,6-Di-O-(2-isocyano-3-methylcrotonyl)-D-mannitol compounds
KR100342789B1 (ko)	2002-07-04	니스타틴에 내성을 갖는 아스퍼질러스속 미생물 및 그를 이용한 트리올 헵타노익산의 제조방법
JPH04243894A (ja)	1992-08-31	新規ｑ−６４０２化合物およびその製造法
US5441987A (en)	1995-08-15	Antifungal agent
KR0184752B1 (ko)	1999-04-01	신규한 마크롤라이드계 항생물질과 그를 생산하는 미생물
JP2576883B2 (ja)	1997-01-29	Ｓ−６３２−ｂ▲下１▼およびｓ−６３２−ｂ▲下２▼物質
JP2856379B2 (ja)	1999-02-10	蛋白質脱リン酸化酵素阻害剤及び抗腫瘍剤
JPWO2001081612A1 (ja)	2003-07-22	ソヤサポゲノールｂの製造法および新規微生物
EP0337548A2 (de)	1989-10-18	Inhibitoren von HMG-COA-Reduktase, hergestellt durch Nocardia SP.(MA6455)(ATCC 53695)
AU2004201294A1 (en)	2004-04-29	Process for the preparation of mycophenolic acid and derivatives thereof
AU2004200673A1 (en)	2004-03-18	Process for the preparation of mycophenolic acid and derivatives thereof
JPS6113798B2 (de)	1986-04-15
JP2001055386A (ja)	2001-02-27	抗生物質ツベラクトマイシンｂ、ｄおよびｅとその製造法
JPH04275284A (ja)	1992-09-30	抗腫瘍性物質ｂｅ−２３３７２ｍ及びその製造法

HUP9903226A2 - Process for producing mycophenolic acid and derivatives thereof - Google Patents

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